ES2536294T3 - Procedure for preparing cyclic diesters, especially dilactide - Google Patents
Procedure for preparing cyclic diesters, especially dilactideInfo
- Publication number
- ES2536294T3 ES2536294T3 ES12190199.5T ES12190199T ES2536294T3 ES 2536294 T3 ES2536294 T3 ES 2536294T3 ES 12190199 T ES12190199 T ES 12190199T ES 2536294 T3 ES2536294 T3 ES 2536294T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- stage
- mixture
- cyclic
- carboxylic acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Procedimiento para la preparación de ésteres cíclicos de fórmula general I**Fórmula** en la que a) en una primera etapa una parte de una mezcla de ácidos carboxílicos oligómeros de fórmula II**Fórmula** en donde en las fórmulas I y II, cada R se selecciona a partir de restos alifáticos lineales o ramificados con 1 a 6 átomos de carbono y en la fórmula II el valor promedio para n se encuentra entre 2 y 40, se convierte mediante despolimerización con ciclación en el diéster cíclico de fórmula general I y el diéster cíclico resultante de este modo de fórmula general I se separa, en donde la parte del ácido carboxílico oligómero de fórmula II que no se convierte en el diéster cíclico de fórmula general I, reacciona durante la despolimerización con ciclación completamente para formar un residuo, que contiene una mezcla de ácidos carboxílicos oligómeros de fórmula II con un valor promedio para n más elevado que en la mezcla de ácidos carboxílicos oligómeros de fórmula II empleados en la primera etapa, b) en una segunda etapa, el residuo obtenido en la primera etapa se hidroliza en una mezcla de ácidos carboxílicos oligómeros de fórmula II, en donde el valor promedio para n se encuentra entre 1 a 20, en un ácido alfa-hidroxicarboxílico de fórmula III**Fórmula** o una mezcla de ácidos carboxílicos oligómeros de fórmula II con un valor promedio para n comprendido entre 1 a 20 y un ácido alfa-hidroxicarboxílico de fórmula III, y c) el hidrolizado obtenido en la segunda etapa se emplea al menos parcial o completamente en la primera etapa, caracterizado por que la despolimerización con ciclación de la primera etapa se realiza hasta que un máximo de 98% en peso de la mezcla empleada de ácidos carboxílicos oligómeros de fórmula II se convierte en el diéster cíclico de formula general I a través de la despolimerización con ciclación.Process for the preparation of cyclic esters of general formula I ** Formula ** in which a) in a first stage a part of a mixture of oligomeric carboxylic acids of formula II ** Formula ** where in formulas I and II , each R is selected from linear or branched aliphatic moieties with 1 to 6 carbon atoms and in formula II the average value for n is between 2 and 40, it is converted by cyclic depolymerization in the cyclic diester of general formula I and the resulting cyclic diester of this formula of general formula I are separated, wherein the part of the oligomeric carboxylic acid of formula II that does not become the cyclic diester of general formula I, reacts during cyclic depolymerization to form a residue, which contains a mixture of oligomeric carboxylic acids of formula II with a higher average value for n than in the oligomeric carboxylic acid mixture eros of formula II used in the first stage, b) in a second stage, the residue obtained in the first stage is hydrolyzed in a mixture of oligomeric carboxylic acids of formula II, wherein the average value for n is between 1 to 20 , in an alpha-hydroxycarboxylic acid of formula III ** Formula ** or a mixture of oligomeric carboxylic acids of formula II with an average value for n between 1 to 20 and an alpha-hydroxycarboxylic acid of formula III, and c) the hydrolyzate obtained in the second stage is used at least partially or completely in the first stage, characterized in that the depolymerization with cyclization of the first stage is carried out until a maximum of 98% by weight of the mixture used of oligomeric carboxylic acids of formula II it becomes the cyclic diester of general formula I through cyclic depolymerization.
Description
E12190199 E12190199
05-05-2015 05-05-2015
mediante eliminación por separación de los contaminantes y es preferentemente superior al 99%, pero en cualquier caso más del 95%. by removal of contaminants by separation and is preferably greater than 99%, but in any case more than 95%.
10 10
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12190199.5A EP2725019B1 (en) | 2012-10-26 | 2012-10-26 | Method for the preparation of cyclic diesters, in particular dilactide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2536294T3 true ES2536294T3 (en) | 2015-05-22 |
Family
ID=47088724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12190199.5T Active ES2536294T3 (en) | 2012-10-26 | 2012-10-26 | Procedure for preparing cyclic diesters, especially dilactide |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9428484B2 (en) |
| EP (1) | EP2725019B1 (en) |
| KR (1) | KR101892580B1 (en) |
| CN (1) | CN104781248B (en) |
| BR (1) | BR112015009181B1 (en) |
| EA (1) | EA027033B1 (en) |
| ES (1) | ES2536294T3 (en) |
| IN (1) | IN2015DN02895A (en) |
| MX (1) | MX361328B (en) |
| WO (1) | WO2014064160A1 (en) |
| ZA (1) | ZA201501651B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2840390A1 (en) * | 2013-08-19 | 2015-02-25 | Mettler-Toledo AG | Coulometric titration cell |
| WO2015156718A1 (en) * | 2014-04-11 | 2015-10-15 | Telefonaktiebolaget L M Ericsson (Publ) | Controlling time division duplex operation |
| EP3130911A1 (en) * | 2015-08-10 | 2017-02-15 | PURAC Biochem BV | Quantification method of meso-lactide in a lactide-containing composition |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2526554A (en) | 1947-07-28 | 1950-10-17 | Goodrich Co B F | Preparation of beta-hydroxy carboxylic acid esters by alcoholysis of linear polyesters derived from beta-lactones |
| US5229528A (en) | 1991-11-22 | 1993-07-20 | E. I. Du Pont De Nemours And Company | Rapid depolymerization of polyhydroxy acids |
| BR9305788A (en) | 1992-01-24 | 1997-02-18 | Cargill Inc | Continuous process for the manufacture of lactide polymers with improved purification methods |
| US5420304A (en) * | 1992-03-19 | 1995-05-30 | Biopak Technology, Ltd. | Method to produce cyclic esters |
| EP0628533A1 (en) | 1993-06-07 | 1994-12-14 | E.I. Du Pont De Nemours And Company | Recovery of hydroxy acids from trash |
| JPH07165753A (en) | 1993-12-08 | 1995-06-27 | Musashino Kagaku Kenkyusho:Kk | Purification of lactide |
| JP3503127B2 (en) | 1995-09-14 | 2004-03-02 | トヨタ自動車株式会社 | Method for recovering lactide from high molecular weight polylactic acid |
| US6229046B1 (en) | 1997-10-14 | 2001-05-08 | Cargill, Incorported | Lactic acid processing methods arrangements and products |
| DE10020898B4 (en) | 2000-04-20 | 2004-02-05 | Inventa-Fischer Gmbh | Process for the production of polylactic acid and device therefor |
| CN100586921C (en) | 2003-12-10 | 2010-02-03 | 塔特和莱利有限公司 | Method for refining lactide |
| US7557224B2 (en) | 2004-04-30 | 2009-07-07 | Kyushu Institute Of Technology | Method for recovering lactide from polylactic acid or derivative thereof |
| EP2072508A1 (en) | 2007-12-19 | 2009-06-24 | Galactic S.A. | Method for obtaining lactide |
| JP2009249508A (en) | 2008-04-07 | 2009-10-29 | Kyushu Institute Of Technology | Method for oligomerizing polylactic acid product efficiently |
| US8394583B2 (en) | 2008-07-24 | 2013-03-12 | The Board Of Regents Of The University Of Texas System | VH4 codon signature for multiple sclerosis |
| CN101434594B (en) * | 2008-12-19 | 2012-05-02 | 河北科技大学 | Method for preparing lactide by mixed solvent process |
| BE1018716A3 (en) | 2009-04-14 | 2011-07-05 | Galactic Sa | CHEMICAL RECYCLING OF PLA BY HYDROLYSIS. |
| BE1019608A3 (en) | 2009-04-14 | 2012-09-04 | Galactic Sa | CHEMICAL RECYCLING OF PLA BY ALCOHOLISIS. |
| BE1018882A3 (en) | 2009-09-10 | 2011-10-04 | Galactic Sa | PROCESS FOR STEREOSPECIFIC RECYCLING OF A MIXTURE OF POLYMERS BASED ON PLA. |
| ES2524988T3 (en) * | 2010-02-26 | 2014-12-16 | Council Of Scientific & Industrial Research | Improved procedure for the preparation of L-lactide of high chemical performance and optical purity |
| CN101906041B (en) * | 2010-08-23 | 2013-07-10 | 孝感市易生新材料有限公司 | Method for producing high-content and high optical purity amyl ester lactate by using two-step method |
-
2012
- 2012-10-26 ES ES12190199.5T patent/ES2536294T3/en active Active
- 2012-10-26 EP EP12190199.5A patent/EP2725019B1/en active Active
-
2013
- 2013-10-23 BR BR112015009181-4A patent/BR112015009181B1/en active IP Right Grant
- 2013-10-23 WO PCT/EP2013/072188 patent/WO2014064160A1/en active Application Filing
- 2013-10-23 KR KR1020157013580A patent/KR101892580B1/en active IP Right Grant
- 2013-10-23 CN CN201380055877.4A patent/CN104781248B/en active Active
- 2013-10-23 IN IN2895DEN2015 patent/IN2015DN02895A/en unknown
- 2013-10-23 US US14/435,640 patent/US9428484B2/en active Active
- 2013-10-23 EA EA201590366A patent/EA027033B1/en not_active IP Right Cessation
- 2013-10-23 MX MX2015005066A patent/MX361328B/en active IP Right Grant
-
2015
- 2015-03-11 ZA ZA2015/01651A patent/ZA201501651B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US9428484B2 (en) | 2016-08-30 |
| BR112015009181A2 (en) | 2017-07-04 |
| EA027033B1 (en) | 2017-06-30 |
| MX361328B (en) | 2018-11-16 |
| EA201590366A1 (en) | 2015-08-31 |
| WO2014064160A1 (en) | 2014-05-01 |
| CN104781248B (en) | 2017-09-12 |
| IN2015DN02895A (en) | 2015-09-11 |
| US20150266849A1 (en) | 2015-09-24 |
| KR20150074159A (en) | 2015-07-01 |
| ZA201501651B (en) | 2015-12-23 |
| BR112015009181B1 (en) | 2020-10-27 |
| EP2725019A1 (en) | 2014-04-30 |
| KR101892580B1 (en) | 2018-08-29 |
| MX2015005066A (en) | 2015-07-17 |
| EP2725019B1 (en) | 2015-04-08 |
| CN104781248A (en) | 2015-07-15 |
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